


Leather & Alcohol.

by doctorkaitlyn



Category: Teen Wolf (TV)
Genre: Age Difference, Alternate Universe - No Werewolves, Explicit Sexual Content, First Time, In which Derek smokes, Loss of Virginity, M/M, One Night Stands, Porn With Plot, Underage Drinking, add a dash of fluff and a dash of angst
Language: English
Status: Completed
Published: 2014-01-12
Updated: 2014-01-12
Packaged: 2018-01-08 11:26:20
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 8,865
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1132079
Author URL: https://archiveofourown.org/users/doctorkaitlyn/pseuds/doctorkaitlyn
Summary: <blockquote class="userstuff">
              <p>Stiles is sixteen years old and fairly inexperienced in the ways of the world when he meets Derek, a drifter who is older by a decade.  Derek's gorgeous, he drives a nice car and, most importantly (at the time), he's willing to buy Stiles and his friends alcohol. </p><p>Derek is only in his life for one day, but it is enough to change Stiles' life forever.  Please read inside for additional warnings.</p>
            </blockquote>





	Leather & Alcohol.

**Author's Note:**

> **Warnings:** In addition to underage drinking, this story contains a sexual encounter that, if I read the laws right, would be illegal in the state of California. As such, I cannot advocate such behavior in real life. 
> 
> However, fanfic is completely different than reality! That being said, if the concept squicks you out or bothers you in any way, it might be best to pass on this story. Otherwise, I hope you enjoy. (:

When Stiles lost his virginity, he was sixteen years old. The man who supplied that service was in his life for just one day and then gone, like a dandelion wisp dancing away on the wind. He never even found out his last name, only the first. 

_Derek._

At sixteen, Stiles and his friends were still five years shy of being able to purchase any booze for themselves and not cool enough to get any of the older students with fake ID's to buy them some. On most summer days, they hung out in the courtyard across from the local liquor store, aimlessly staring, occasionally reminiscing about the few sips of alcohol they'd tasted in the past. Every adult they managed to get the courage up to ask gave them dirty glares, with some of the real hard asses threatening to call the cops. Even the resident potheads said no, ruffling their hair and sauntering off, leaving the stink of marijuana to linger as a reminder of their initial rejection.

It was a blisteringly hot day in July, the Beacon Hills humidity so thick it was almost suffocating, when the course of Stiles' life was changed forever. Even in the shade, there was little relief and sweat poured freely off of his face. He was lying on his back with his head in his friend Scott's lap, arm thrown over his face, wishing that he'd stayed home in the air conditioning. 

"We should go swimming," Isaac muttered from where he was lying beside Scott, his usual endless amount of energy zapped. "The lake's not that far away."

"Still too far away to walk," Stiles groaned, wiping his forehead. "I'm not moving until it's not so fucking hot."

"I could go for a beer," Scott said, making both Isaac and Stiles curse as their dry mouths salivated at the thought of some ice cold _anything_.

"Don't be a tease." Isaac rolled onto his stomach, resting his head on his arms and Stiles couldn't help but roll his eyes at the obvious double entendre. "Especially not on a day like this."

"There's a guy over there," Scott replied casually, making both Stiles and Isaac sit up and look across the street at where Scott was pointing to the man leaning up against the brick wall of the liquor store, smoking a cigarette and wearing a leather jacket despite the sweltering heat. His black hair was spiked up in the front and Stiles was pretty sure he had to have used industrial strength hair gel, since it didn't show any signs of drooping.

"Go ask him," Scott said, elbowing Stiles purposefully. Stiles snorted and shoved him over, gaze still drawn to the mystery man. The man looked just a little too old to be in high school still and Stiles didn't recognize him from any of the old yearbooks he'd casually flipped through when he was bored in the guidance office. Beyond that, he didn't recognize him from any of the mug shots his dad had showed him, which meant there was a high chance that he wasn't from Beacon Hills at all. For some reason, in Stiles' mind, that seemed to mean that there was a higher likelihood of him buying them booze. However, the fact that the guy was just lingering outside of the liquor store, apparently in no hurry to go anywhere, was kind of suspicious and Stiles didn't really feel like getting kidnapped, not today.

Unless the kidnappers had an air conditioned van. He'd be willing to consider if that was the case.

“What 'bout Allison?” he asked, lying back down on the grass since Isaac had stolen his previous spot in Scott's lap. “If you guys are so determined to drink, why don't we just go over there?”

“She's training all day,” Scott said, him and Isaac sighing in sync, cuing another roll of Stiles' eyes. Stiles had absolutely no problem with the fact that his three best friends were perfectly content to be entangled in a three-way relationship but sometimes they fawned over each other with such profoundness that it made him a little queasy. 

"Stiles, if you don't ask him, I'll tell Heather you dumped her because she couldn't make you hard." Isaac and Scott both snickered at the effect the threat had; Stiles could feel his face turning red (without his permission) and he jumped up, brushing his jeans off with his hands.

"First off, that's not the whole truth and second, fine, I will ask, because you two suck." Isaac winked at him and Stiles groaned again before taking off. Even walking the short distance from point A to point B made sweat spring up on the back of his neck and he wiped it off futilely. His lips were cracked and licking them didn't help at all, although he realized that he probably looked like he was trying to be seductive. Apologies were already running through his mind but by the time he picked one that actually made sense, he'd reached the leather-clad dude that he was designating Mystery Man until he was provided with another title.

"Hey." He hadn't even noticed until he was right in front of him that the man was looking at him over the top of his aviator sunglasses, smirk playing at the corner of his mouth. 

"Hi." His voice wavered slightly and he shook his head, leaning against the wall and trying to look as casual as possible. In the courtyard, he could see Scott and Isaac trying to look inconspicuous and failing; even from across the road, Stiles could hear them laughing like complete fools. 

Bastards. 

"What are they laughing about?" The man's cigarette dropped to the ground between them and a scuffed up sneaker stubbed it out, grinding it to dust.

"Okay, I'll be honest," Stiles said, giving up on trying to look cool or suave because if the continued laughter was any indication, he looked like an absolute moron. "My friends want someone to buy us booze and I got suckered into asking you if you would." He reached into his back pocket before he received a response and thumbed through his wallet, mouth moving as he counted his money, aware in the back of his mind that he was going to have to concoct some sort of story to explain to his dad how he'd gone through it all in one day.

"Here's fifty dollars," he said, handing him every bill he had in his wallet. "If that's not enough, Scott's got a job and I'm sure he can pony some up and..." He stopped talking, face turning red at the chuckles that were being directed his way, although these ones were coming from Mystery Man, as opposed to his friends. The man took off his sunglasses and pinched the bridge of his nose, continuing to chuckle. When he looked back up, Stiles got a good glimpse of the man's eyes and the sight actually made him take a step back. Sure, he may have had a bit of an overactive imagination but that didn't mean he was stupid; he was all too aware of what was lurking in Mystery Man's green eyes, recognized it from when Scott or Isaac got a glimpse at some of Allison's more revealing outfits. 

_Lust._

"Put your money away," he said, shoving Stiles' still outstretched hand away. "If you guys are that desperate for some alcohol, I'll get you some." He was still laughing when he entered the liquor store, a brief puff of beautiful cold air reaching Stiles' skin before being cut off by the door. Stiles pushed his palms into his eyes and slid down the brick wall to the asphalt, groaning and mentally berating himself for looking like a complete fool. He knew that sitting on the tarmac right outside the store probably wasn't the best idea in the world but frankly, he wasn't willing to leave the small patch of shade he'd hunkered down in. Besides, they'd been watching the store for hours and all things considered, it had been a pretty slow day. If anyone did decide to stop by, he'd just lie his way out of it and hope that they didn't call his dad. 

As it was, he had nothing to worry about. Nearly ten minutes passed without a customer coming to or leaving the store and he was starting to think that Mystery Man had escaped out the back door, which would have been even more humiliating. Isaac and Scott would never let him leave it down and he was actually surprised neither of them had gotten up to see what was going on. He flicked his eyes up from the tarmac, which he'd been staring at nearly the entire time and returned them there almost as quickly. Apparently Isaac and Scott had found a more interesting way to spend their time; he'd only gotten a split-second glimpse at them but he was about seventy percent certain that Isaac's hand had been in Scott's pants. 

“Damn over-sexed teenagers,” he muttered to himself and, speaking of his own raging hormones, he felt another blast of cold air as the door opened, revealing Mystery Man holding a black tote bag that looked like it would split open at any moment. It brushed against Stiles' face as the man passed and he shivered, briefly pressing his skin against the retreat from the heat. He scrambled to his feet, blushing at the eyebrow Mystery Man had raised at him. That same little smirk had returned to his lips and Stiles was pretty sure the man was the only person he'd ever seen who could pull off _you're ridiculous_ and _I want you_ at the same time. At least, that was how he was reading it. Maybe the heat was just sending him into hallucinations.

"Cold enough for you?" He nodded and looked across the street at Scott and Isaac, who had stopped making out and weren't bothering to hide their wide eyed staring.

"Thank you," Stiles said, trying his best to hold his own against that goddamn piercing stare. "Really, thank you."

"Where do you plan on drinking this?" the man answered, gently tapping the loaded tote bag against his leg. Stiles shrugged, waving his arm vaguely in the direction of the courtyard.

"Probably over there in the shade. Why?"

"Do you think you'll be able to do that without being caught?" Stiles shrugged and in response, the man snorted and switched the bag to his other arm, moving it out of Stiles' reach. "It may be a slow day but if that guy in there sees you three drinking, to the drunk tank you go." He pulled another cigarette out of his jacket pocket and stuck it between his lips, leaving it there like an obscene lollypop and oh lord, there was no stopping Stiles' imagination now. 

"Well, do you have a better idea in mind, Mystery Man?" he asked, feeling an unexpected surge of confidence come over him. It was immediately followed by a rush of embarrassment as he realized what he'd actually said. Thankfully, the man seemed to take it in stride; he merely chuckled again before hoisting the bag up onto his shoulder, cigarette still clamped between his teeth.

"Go get your friends," he said, gesturing across the road to where Isaac and Scott were practically drooling over the promise of cold alcohol (or maybe it was each other, Stiles really didn't know). "We'll head to the beach or something." Stiles grinned, already halfway across the road.

"Hey, what's your name?" Mystery Man yelled, pausing in front of the only vehicle in the lot, a shiny black Camaro that looked like it was hardly a day off of the assembly line.

"Stiles."

"Derek."

***

Derek drove with a recklessness that made Stiles wonder how he'd passed his driving test, one hand clutching the steering wheel and the other holding a cigarette. The bag of alcohol sat between Stiles' feet on the floor, loudly clinking whenever Derek rounded a corner. In the back, Isaac and Scott were alternating between giggling and looking around in awkward silence, obviously wondering if this strange man was going to drag them off and murder them.

"How old are you guys anyways?" Derek asked, glancing up into the rear view mirror and skidding around a corner at the same time.

"Sixteen," Stiles answered, earning another giggle from the back seat.

"A little young to be drinking, aren't you? What would your parents say?" 

“They trust us not to make bad decisions,” Scott piped in, his arm loosely draped over Isaac's shoulder. “Besides, my mom and Stiles' dad both work tonight. They'll assume we're with each other.”

“Which isn't a lie,” Stiles quickly said. His eyes drifted over to Derek again and he found himself staring at his hands, wondering what his fingertips would feel like roving over his body, what it would be like to have them wrapped around his wrists, holding him down and leaving bruises behind. 

“Besides, what they don't know won't kill them.” In the backseat, both Scott and Isaac chuckled, but Stiles knew it had nothing to do with the way he was looking at Derek and everything to do with the way they were looking at each other and he really wanted to mutter _calm your damn hormones_ to them but that would have made him the worst kind of hypocrite. 

"I suppose that's true." Derek was smirking _again_ and Stiles got the sudden urge to lean across his seat and wipe it off his face with his lips, smother it with a kiss. Instead, as Derek pulled into the miraculously empty parking lot near the beach, Stiles grabbed the bag of alcohol from his feet and got out of the vehicle as fast as he could, feeling the sexual tension disappear like dust into the open air. Down by the water, the heat wasn't nearly as bad and the small breeze coming off the water felt like pure and absolute heaven. Isaac had already stolen a bottle of vodka from the bag and was lying in the sand, sipping it slowly, his face contorting with each gulp.

"Calm down Isaac," Scott said, gently tapping him in the ribs with his foot as he settled down beside him. "If you puke, that's some good alcohol wasted." The sand was cool underneath Stiles' flushed skin and he rested his head on his arm, pulling a random bottle out of the bag and claiming it as his own. The sand shifted beside him and he glanced up, feeling his stomach twist when he found those green eyes staring at him again, like an animal stalking their prey.

By all rights, he knew that he should have been unnerved by that look but considering he was pretty sure he'd been leching at Derek for the entire car ride, he really couldn't say anything about it. 

'Hey, uh, thanks for the booze man," he said, averting his eyes. Unexpectedly, he felt Derek's callused fingers brush over the back of his hand and even as he willed it not to happen, he could feel himself blushing again.

"Don't worry about it."

***

By the time that the sun finally went down, their supply of alcohol was pretty well exhausted, leaving Isaac and Scott both stumbling drunk. Stiles had been nursing the same bottle of whiskey all night and, aside from an odd feeling in his eyes, he felt perfectly fine. He hadn't seen Derek drink at all; he only smoked cigarette after cigarette, to the point where Stiles was wondering how the hell he hadn't run out.

"Stiles!" Scott yelled, tripping over a stick and falling to the ground. For at least five minutes, he simply lay there, laughing hysterically at seemingly nothing. Isaac was sitting near the water, toes burrowed in the mud, talking about how beautiful the scenery was.

"Oh Stiles, I love you," he finally groaned, sitting up and falling with his head in Stiles' lap. "Please don't be mad at us."

"I'm not mad at you," he sighed, trying to subtly maneuver Scott's head away from his crotch. "I'm not mad at Isaac either."

"Good. Good." He sat up and gave Stiles a sloppy, wet kiss on the cheek and although Stiles didn't mind the sentiment, he did mind the saliva that was smeared on his face. Scott had just pulled away when his phone went off and he rolled over onto his back, holding it above his face. 

“Isaac!” he yelled suddenly, yelping quietly as he dropped his phone directly on his nose. “Allison says she can meet us at the preserve!”

“Really?” Isaac scrambled to his feet (and only managed to stumble once, which Stiles thought was impressive), face lit up with a giant goofy grin. “Stiles, do you mind if-”

“No, guys, go,” he said, coughing as his latest sip of whiskey went down the wrong way. “Please, enjoy your night with Allison.” The words had hardly left his mouth before both of his friends were taking off down the beach. They yelled _thanks!_ over their shoulders before they had vanished into the woods that lined the beach. Stiles knew that he was probably being an irresponsible friend by letting them wander off by themselves, especially in their intoxicated states, but the entire night, Derek had been shifting closer and closer and even now, he could feel his fingers almost on top of his own. 

"Do you want a cigarette?" Derek's voice was right by his ear and he jumped, nearly sprawling on his back. Derek already had a smoke dangling between his lips, with another clutched between his fingers. Stiles had never even considered smoking but he plucked the cigarette from Derek's hands and slid it between his lips, lightly probing it with his tongue. A tongue of flame briefly flashed and then he was coughing, hissing as he burned himself on the glowing end, coughing until he swore his lungs were going to come out of his throat.

"I didn't like that," he choked, throwing it into the sand. "Fuck, I didn't like that at all." Derek only chuckled and shifted even closer, sliding his hand up Stiles' forearm, sending a shudder through his body that he tried to disguise with a faked sneeze.

"Beautiful night," he said weakly, shivering again as Derek's fingertips dragged over the thin skin on the inside of his wrist. 

"Perfect time to go swimming." Derek stood up and slid the leather jacket tenderly to the ground, treating it more like a piece of gold than the piece of clothing it was. Stiles couldn't help himself from staring, his eyes fixated on Derek's outline against the sky. It was only when the buckle for Derek's belt hit him in the foot that he stood up as well, pulling his thin t-shirt over his head and shivering as the cool air touched his bare chest. He stepped out of his shoes and socks but left his jeans on and even then, he could feel Derek's eyes looking him up and down.

"C'mon." Derek's jeans were still on as well but without the belt holding them up, they were sliding down to rest on his hips, revealing the elastic of his underwear. It made Stiles' body grow warm despite the cool temperature and he shuddered again before running and plunging into the cold water, feeling his heart skip at the shock. When he popped up, wiping water away from his eyes, Derek was nowhere to be found. The only sound was the waves gently lapping against the shore and when Stiles glanced around, he couldn't see him anywhere.

He stood up fully, the water coming to his belly button, tickling the fine patch of dark hair that was barely visible trailing down underneath the top of his jeans. A full moon lit up the night sky and he took advantage of it, gazing at the nearby water to see if he could see Derek swimming underneath because with each second that ticked by, he was starting to worry more and more.

When the cold hands first touched his waist, he jolted, gasping loudly enough to shatter the silence that surrounded them. Derek's fingers were cold but their movements were hardly perceptible, brushing like feathers before they disappeared again. The next time he felt them, he curled his fingers around Derek's wrists, keeping them there. It was one of the nicest feelings he had ever experienced but it only intensified when Derek started kissing his neck, starting with the hollow under his ear and moving down his throat. Bolts of pleasure coursed thorough his body and his fingernails scratched at Derek's hands, leaving red trails behind as he just tried to stay on his feet.

Stiles didn't even know _how_ they ended up on shore again but they did, the sand grinding underneath his still-bare back, his hands grasping for any part of Derek he could reach. He didn't have a fucking clue what he was doing because aside from some quick fumbles with Heather and Danny, this was all brand new but Derek didn't seem to care, based on the quiet curses he murmured every so often. Stiles tasted blood in his mouth for a moment but the next, he was swept away in another whirlwind of kissing and touching and gasping and cursing.

"You know this is illegal, right?" Derek whispered in his ear, letting out a little gasp as Stiles danced his fingers along Derek's waist, slipping underneath the waistband of his boxers.

"Why?" Pressing against Derek's legs with his knees, he switched their positions, mouth instantly attaching to Derek's neck as he tried to duplicate the pleasure he had received in the water. He'd barely started nibbling when Derek pulled him up, a hand firmly pressed to either side of his face.

"I'm 26," he said quietly and Stiles' body froze for a moment as he quickly ran the situation through his head. He knew that if the wrong person found out, Derek would be sent to jail and he barely even knew the man but he definitely didn't want him in jail, especially since that was bound to lead to _so_ many uncomfortable conversations with his dad. But at the same time, he was so fucking horny that if he didn't get off soon, he thought he might just die of blue balls and personally, he felt like that was a pretty lame way to go.

Besides, what he'd said earlier still applied: what his dad didn't know wouldn't kill him. 

"I don't care," he groaned, rolling his hips downward, nails digging into Derek's shoulders. "I just want you so goddamn badly, please Derek, _please_."

"Okay," Derek murmured after a moment, his hands sliding from Stiles' face to the back of his neck. “Let's get out of here then.”

***

Although Stiles had thought that Derek had been driving recklessly in daylight, that was nothing compared to how he handled the Camaro once the sun had gone down. The clock on the radio said two in the morning, the roads were empty and Derek was flying around turns like James Dean, like he had a death wish. Only one of his hands was actually on the steering wheel; the other one was clutching Stiles' thigh tightly and Stiles was pretty sure that between Derek's bruising grip and the still-damp state of his jeans, the pattern of the seams was going to be imprinted in his skin.

As Derek went around a particularly sharp corner at a frightening speed, Stiles tried to resist the urge to ask him to pull over. It was a multifaceted urge; even though it was so late (or so early, Stiles didn't really know), he figured it was almost certain that they would pass one of the cops coming in the opposite direction. Hell, there was a good chance that it would be Stiles' dad and he really didn't want to be grounded for the remainder of the summer, not to mention the multitudes of other problems he'd be facing. The other part of the decision was highly influenced by his dick, which was _still_ hard and pressing rather uncomfortably at his zipper. Even though they were starting to enter the more populated areas of Beacon Hills, he really wanted Derek to just pull over and drag him into the back seat. 

However, his brain managed to communicate the many reasons why that wasn't a good idea so instead, they were flying like bats out of hell to the motel room Derek owned for a night. Stiles' stomach was knotted, not just from the excessive speed but because he knew what was unavoidably about to happen and he couldn't help but wonder if it would hurt, if it was going to feel as good as he hoped.

They skidded into the parking lot, nearly hitting another car that had already had its fair share of dings. The instant he stepped out into the air and shut the door, Stiles found himself pinned to the side of the car, nose filled with the smell of Derek's jacket, his hands grasping at still damp skin. When Derek moved away from his mouth, he only went as far as his neck, sharp teeth pressing into the dip of his throat and Stiles was pretty sure that he was babbling but given the circumstances, he was also pretty sure that his babbling was okay. 

They somehow managed to break away from the car long enough to actually get into the room but as soon as the door was closed, Stiles' back was slamming into it. Derek kissed like he was running away from something and truthfully, Stiles didn't mind helping him with that. Stiles only pulled away when he needed to breathe and even then, Derek didn't stop; he grabbed Stiles' arms and pinned them above his head, undoubtedly leaving bruises on his wrists, just like Stiles had fantasized about hours ago.

“You are beautiful,” Derek murmured against his neck, dragging his teeth down until they caught against Stiles' collarbone. “God Stiles, _perfect_.”

“ _Derek.”_ There was so much going through Stiles' brain, so much that he wanted to say but when he tried to express it with words, all he could get out was Derek's name. As much as he was enjoying the attention Derek was paying to his neck, the bed was beckoning and he reluctantly pushed away from the door, sending Derek across the small space and onto the lumpy mattress that was probably already splashed with cum (and eugh, that was not something he'd been planning on thinking about). Derek reached out to grab at his hands but Stiles wrenched his wrists away, buzzing with adrenaline and confidence. 

"Jesus Stiles," Derek said quietly, wetting his lips and leaning back on his elbows. Stiles slowly pulled his shirt over his head, savoring the way Derek's eyes got a little bit bigger as it dropped to the floor with an almost inaudible noise. He started to fiddle with the button on his pants but before he could even think of undoing it, Derek was moving again, growling impatiently. Before he could say anything, Derek's lips were on his stomach and his hair was brushing against his ribs. Stiles' pants were feeling _way_ too tight and as if his mind had been read, they were on the floor and Derek was pulling him onto the bed so that he was straddling him in only his thin boxers. Derek, on the other hand, was still wearing all of his clothes and that was a problem Stiles planned on solving as soon as he could. 

"Need to get some of your clothes off," he panted, trailing his fingers down Derek's chest, fisting them in the fabric of his shirt. In response, Derek sat up, Stiles still in his lap and pulled his leather jacket off, tossing it off to the side with such force that it almost took out the lamp he'd turned on. That was quickly followed by his shirt and when Stiles trailed his hands down Derek's back, he could feel the raised lines from where he'd scratched earlier. He ran his nails over some of the more prominent ones and Derek growled again, his hands sliding down to squeeze Stiles' ass and Stiles was pretty sure that he was going to wake up from a dream at any moment because there was no _way_ this was happening. 

“Hold on,” Derek said and before Stiles could really question the statement, Derek was flipping them over. The bed was unpleasantly firm underneath his back and the smell of old detergent was horribly pungent in his nostrils but really, none of that mattered. The next few minutes were a whirlwind of wandering hands and bruising mouths and Stiles didn't really remember when or how Derek had lost the remainder of his clothing but what he _did_ know was that their cocks were rubbing together and it felt absolutely heavenly and he had the rather alarming thought that if they didn't slow down, he was possibly going to finish before they even really got started.

Thank God for small favors because almost immediately after the thought appeared in Stiles' head, Derek pulled back, his lips red and swollen, hair a tousled mess. His hand tightened on Stiles' hip and Stiles made a note to count his bruises when he woke up the next day. 

"Is this going to be your first time?" Derek asked and the expression on his face was so much more than mindless lust. It was _want_ , the kind that carried more than physical meaning and if Stiles was being honest, it was more than a little overwhelming. The thought that this might be just a drunken fuck vanished, all because of that look in Derek's eyes.

“Uh no,” he stuttered. “I mean, yes. I don't know why I just lied to you. Yeah. It will be.”

“Do you want me to stop?” Derek pulled back even further, brow furrowed and Stiles propped himself up on his elbows in order to fill the empty space between them. 

“No. Please, Derek. I want this, I want _you_ and I definitely don't want you to stop.” Derek exhaled slowly before pulling Stiles into a kiss that seemed far too intimate considering the circumstances. Something had changed, something in the air itself and although it definitely complicated things, Stiles couldn't help but admit that it did make him feel better about losing his virginity to a near-stranger on a cheap motel bed. 

"I'll be right back," he whispered against Stiles' mouth when he pulled away. “Gotta go some stuff, okay?” Stiles nodded, stealing one more quick kiss before Derek slid off the bed, disappearing into the bathroom. Stiles closed his eyes and ran his hand down his chest, his cock aching in a way he'd never experienced before, not even on the occasions he'd woken up from an absolutely _filthy_ dream starring-

Derek was back and Stiles opened his eyes again, taking in the small bottle of lube and the condom he was sitting on the bedside table. This was happening, this was _actually_ happening and he forced himself to take a deep breath before he started hyperventilating. Derek grabbed one of the nearby pillows and Stiles lifted his hips off of the bed so that he could lower himself down on it. This part didn't really scare him; he'd watched enough porn (like, an obscene amount of porn, frankly) and done enough research to know how prepping generally worked. 

“You nervous?” Derek asked, popping the cap on the lube and dripping it over his fingers. Stiles shook his head because even if he wasn't nervous and wasn't scared, his ability to talk was, for once, compromised. In response, Derek tossed the bottle aside and moved back between Stiles' legs, leaving stray droplets of lube on the sheets. His dry hand settled itself on Stiles' hip, thumb moving back and forth over the bone while his slicked-up fingers ran down over Stiles' cock. 

“Lift your legs a little bit,” Derek murmured, his eyes fixed between Stiles' legs and Stiles did as he was asked, trying steadfastly to ignore how awkward and exposed he felt. The change in position seemed to be what Derek was looking for because one of his slippery fingers trailed down further until it was gently pressing against Stiles' hole. 

“You ready?” he asked and Stiles was pretty sure that if Derek held off any longer, he was going to sob from pure frustration. Apparently he'd said that out loud because Derek was leaning up to kiss him, muffling Stiles' gasp when Derek's finger pushed in. He wasn't exactly new to this, had spent numerous nights fucking himself on his fingers but Derek's were thicker, felt different, felt _better._ He tried to push his hips down so that he could have more but Derek was still gripping him tightly, holding him right where he was. 

“I don't want to hurt you,” he said, scraping his teeth over where Stiles' jaw met his throat before he sat back on his knees and all Stiles could do was whine because this was downright cruel. Derek finally pushed the rest of his finger in and before Stiles could even say _fucking finally_ , he was teasing the tip of his second finger around his rim. Just teasing, but it was enough to make Stiles curse and bury his face in the other pillow. 

“You suck,” he muttered, groaning as Derek stopped teasing and pushed in his second finger. 

“Maybe next time,” Derek said above him and _Jesus_ , Stiles didn't think it should have been possible for one sentence to nearly make him come. 

Unlike his death-wish driving, Derek's preparation was slow and methodical; he took his time, curling and twisting his fingers, running his other hand over the inside of Stiles' thigh and his stomach and his cock. By the time he had three fingers buried inside, Stiles was covered in sweat and reduced to a begging, babbling mess. There was an element of burn still present when Derek stretched his fingers out but it was easy to bear. 

“Derek, please, goddamn it, I've been ready for five fucking minutes, are you _trying_ to kill me?” 

“You're over dramatic,” Derek replied but notably, he did withdraw his fingers, reaching for the condom. Before he could actually open it, however, Stiles snatched it out of his hands because frankly, he thought it was a little bit egregious that he hadn't touched Derek's cock with his hands yet. He tossed the wrapper aside but before he unrolled the condom, he ran his thumb down Derek's dick, smearing the pre-cum that had gathered on his head down the rest of his shaft. Derek's hand came up to rest on the back of his head, running over his scalp slowly and when Stiles gripped him so that he could unroll the condom, the older man full on moaned, dropping his head down to his chest. 

“Did I do that right?” he asked once the condom was on, internet instructions still present in his mind. 

“Perfect,” Derek said and with one quick movement, Stiles was on his back again, his knees brought up to his chest. Derek pressed his fingers in again briefly, crooking them a few times before he wiped them off on the sheets and lined his cock up with Stiles' hole. 

“Ready?” Stiles nodded once and then there were little tendrils of pain spreading through his ass and his lower back as Derek slowly pushed in. Nonetheless, it was bearable pain, pain he'd expected and he tried to breathe deeply, adjusting his legs so that they were wrapped around Derek's back. 

"Do you want me to stop?" Derek asked, his face full of concern and Stiles shook his head, taking another deep breath and adjusting his legs a little more. 

“No, don't you dare,” Stiles said, digging his fingernails into Derek's shoulders. “I'll be okay. Keep moving.” Even though Stiles had thought he'd sounded pretty genuine, Derek still looked worried and the best solution Stiles could think of was to kiss him as hard as he could, tangling his fingers into Derek's hair and running his tongue over his lips. That seemed to do the trick; Derek pushed in further until his hips were flush with Stiles' ass. The feeling was nothing in comparison to Stiles' fingers; he had never felt this full, felt so stretched and when Derek shifted even slightly, the movement sent shivers up his spine. 

It took Derek a few moments to set a steady pace but once he started moving, he _really_ started moving. The pain had been banished and all Stiles could feel was complete and utter bliss. He was pretty sure that his heels had left bruises on Derek's back and he could see nail marks in his shoulders and when Derek leaned down to nip at his earlobe, Stiles turned his head and sucked a hickie into his throat. Derek's thrusts were so powerful that they were making the thin headboard slam into the wall and Stiles _really_ pitied whoever was staying in the adjacent room. However, Derek's thrusts had also pushed Stiles off of the pillow that was holding his hips up and after a moment of awkward fumbling, he growled in frustration and pulled Stiles up into his lap, only slipping out for a second before he was back inside, gripping Stiles' upper thighs so that he had leverage to continue his relentless pace. Although Stiles hadn't expected the switch-up, he certainly wasn't complaining because with every thrust, Derek was rubbing against that bundle of nerves inside of him and he was pretty sure that his eyes were rolling into his head.

“Jesus Christ,” he panted, tightening his legs around Derek's waist, hoping that his quavering muscles would hold on for a few more minutes. 

“Are you okay?” Derek asked, gasping against Stiles' shoulder when Stiles made an attempt to roll his hips down to meet Derek's upward thrusts. 

“I'm fucking great.” That was no understatement; Stiles' cock was rubbing against Derek's abs, gliding through sweat and pre-cum and although the friction wasn't enough to make him see stars, it was certainly doing a good job of getting him there. His legs were starting to tremble more and more with each second that passed and with each one of Derek's thrusts, he could feel himself creeping closer and closer to the edge. 

“Stiles, you can touch yourself if you want,” Derek panted against his ear, voice hitching and if Stiles was correct, Derek was trying to hold himself back. 

Well, making him wait any longer would have been rude so, leaning back a little so that he had enough room, Stiles grasped his cock and tried to match his strokes to Derek's thrusts. Between his own hand and Derek's cock and Derek's teeth pressing into his shoulder, it was only a few moments before he was coming on his fingers and his chest, head thrown back towards the ceiling, eyes slammed closed. 

“Stiles!” He hardly had time to suck in a breath before Derek was slamming into him hard enough to knock the air out of his lungs, mouth dragging over the already marked up skin on his throat and his collarbone. His hips stuttered once, twice, three times before he stiffened up, teeth sinking into Stiles' shoulder. Ever after Derek came back down, he made no attempt to move for at least a moment and even though the trembling in Stiles' muscles had progressed to a steady, painful throbbing, he didn't try to get up. Derek was panting against his shoulder and had slid his arms up to wrap around Stiles' back and even though Stiles felt like his ribs were slowly rearranging themselves underneath the pressure, he liked the contact too much to complain. After another few moments, Derek exhaled slowly and set Stiles down on the bed, slowly pulling out and dropping the condom in the garbage beside the bed. 

“Are you okay?” he asked and Stiles took a moment to do a quick inventory. His neck and shoulders were positively throbbing (he didn't even want to think about how they were going to look in the morning), he was pretty sure that walking was going to prove difficult and the inside of his thighs was sticky with lube and sweat. 

But that was only physical. Emotionally, he felt fucking fantastic. Maybe it was just leftover hormones and adrenaline but he didn't really feel like analyzing it any further because he was _happy_ , plain and simple. 

“Yeah Derek,” he said quietly, idly kicking the pillow that had been underneath his hips off the bed. “I feel great.” 

“Good. That's good.” Derek leaned down and kissed him quickly before he stood up, stretching his arms above his head until his back cracked. He ducked into the bathroom quickly and came back out with a dripping washcloth. 

“Don't you even think about moving,” he said, effectively banishing any thoughts Stiles had about asking for a ride home. “I'm just gonna have a smoke.” 

“'kay.” Derek pulled on his jeans and left, smoke already clamped between his teeth and Stiles was pretty sure that if it hadn't been for the weariness and pain seeping into his limbs and brain, that image would have been enough for him to get it up again. As it was, his cock only twitched slightly while he was cleaning himself off and when he was done, he tossed the washcloth in the general direction of the bathroom. By the time Derek came back inside, he had managed to kick the sheets off as well; they were practically drenched in sweat and stray droplets of lube and Stiles _really_ felt bad for the poor cleaning crew. 

“Still feeling okay?” Derek asked, shucking his jeans off again and brushing his hair away from his forehead. Stiles nodded and opened his mouth to respond, only to yawn like an absolute moron. Derek just chuckled and switched the light off. When Stiles felt the mattress dip slightly underneath Derek's weight, he started wondering if the bed was actually going to fit them both and if Derek could procure another pillow from somewhere but then Derek's fingers were closing around his wrist, thumb stroking over his pulse. 

“Come here.” Derek's voice was a lot softer now and it was actually a little difficult for Stiles to reconcile his tone with the way he'd sounded earlier, when he'd been panting Stiles' name. Stiles certainly wasn't going to protest Derek's request; he scooted over until he was lying on Derek's chest, arm slung over his waist. Derek's hand was resting between his shoulder blades, fingers slowly tracing patterns into his skin and even though Stiles was experiencing some major cognitive dissonance (this was _not_ how one night stands were supposed to work), he wasn't going to deny just how wonderful it felt. 

“Can I ask you something?” His eyes had already drifted closed but his mind wasn't quite ready to stop working yet. 

“Sure.” 

“What were you doing at the liquor store earlier?” Derek chuckled, his fingers skating along the back of Stiles' neck.

“Actually, I was just finishing my cigarette before I got some beer. So you're lucky you came across the road when you did, or...” Derek trailed off and truthfully, Stiles didn't really know how to finish the sentence either because really, what _were_ you supposed to say to that? Were you supposed to say something like _or I wouldn't have lost my virginity tonight?_

He really didn't want his mouth to ruin what had been a nearly perfect evening so instead, he tightened his grip on Derek's hip, found a comfortable position for his other arm and let himself sink into the mattress. The last thing he remembered was the steady noise of Derek's heart underneath his ear and even though on some level he knew it was an absurd thought, he could have sworn that it was saying his name with every beat.

_Stiles, Stiles, Stiles._

***

When Stiles woke up, the sun was shining directly in his eyes and he winced, slamming them shut again. It was only then that he was aware of the absence of Derek's heartbeat underneath his head and he sat up, immediately spotting him in the small room. He was sitting at the small table underneath the single window, fully dressed, cigarette smoke trailing out behind his ear like a scarf caught in the wind. There was a red-purple bruise flourishing on the side of his neck and Stiles couldn't help but smirk because Derek had been hot before, no doubt about it, but Stiles thought he preferred him marked up, so long as those marks were from his mouth. Derek was staring out the window, like he was deep in thought but when Stiles cleared his throat, he jumped up from his seat, as if he'd been caught doing something naughty.

Stiles supposed that, technically, having sex with jailbait (not a term he really liked, but the truth nonetheless) _was_ something naughty but if that was what he was so jumpy about, the man had changed a _lot_ in only a few hours. 

"We should probably get you home," he sighed, rubbing the back of his neck. "It's already noon." Stiles just nodded and leaned over to pick his pants up off the floor, barely biting back a groan at the bolt of pain that wriggled up his spine. He expected Derek to lean over and help but he just stood there, scratching the stubble on his jaw and glancing anxiously towards the window.

Stiles had barely pulled his t-shirt back on before Derek grabbed his wrist, tugging him out the door towards the Camaro. Sitting down in the passenger seat hurt a little more than he anticipated but he hardly had time to concentrate on the pain because Derek was tearing out of the parking lot before he'd even gotten his seat belt on. As Derek rounded a corner with particular viciousness, Stiles' head bounced off the window and he hissed, pressing his fingers to the sore spot on his temple. There was definitely something wrong; Derek had hardly said a word the entire time and when Stiles looked over, his fingers were wearing grooves into the leather cover of his steering wheel. 

"Derek?” he asked, raising his hand before he thought better of it and tucked it back into his lap. The last thing he needed was Derek lashing out at him and getting them into an accident. 

"You're just a fucking kid," he whispered, eyes staring straight out the windshield. One of his hands uncurled itself from the wheel and he pressed it into his thigh, nails scraping at the denim of his jeans. "You're just a fucking _kid_ that I took advantage of."

"Derek, it was consensual-"

"That doesn't matter!" In an instant, the volume of Derek's voice increased tenfold and Stiles instinctively pressed himself against the passenger door. A single tear dripped out of Derek's eye and he wiped it away hard enough to leave scratches down his cheek. "You're sixteen! You could be my younger brother, for Christ's sake!"

"I'm not a goddamn kid!" Stiles yelled back. The night before felt like nothing more than a dream now and Stiles squeezed his eyes shut until his own tears fucked off. "I could have stopped you at any time but I _wanted_ it!"

"You were wasted, Stiles-"

"I wasn't fucking drunk, Derek.” Derek opened and closed his mouth a few times before just sighing, running a hand through his hair, cursing underneath his breath.

“Where am I taking you?” he finally said and Stiles could tell from the set of Derek's jaw that he was deliberately trying not to look over at him. The foolish side of him wanted to grab Derek and _make_ him look at him, _make_ him come to his senses but Stiles had a feeling that, aside from being dangerous, it wouldn't work. So instead, he told Derek to turn right at the next intersection and leaned his head against the window, wincing slightly every time his bruised temple bumped against the glass. He didn't want to go home; his dad would still be sleeping because of the previous night's shift and truthfully, Stiles knew that he'd have to find some way of covering up the numerous bruises along his throat before he saw his dad again. He was pretty sure that Isaac and Scott had some experience in that area and besides, he needed someone to take his mind off of... well, off of whatever the fuck had happened. 

But even as Derek pulled into the driveway behind Mrs. McCall's car, he couldn't just take off and leave because, whether or not Derek wanted to admit it, Stiles knew that something important had happened between them, something that went beyond a mere one night stand. He had absolutely no idea how to describe it but he was certain of its existence. Apparently Derek was thinking the same thing because he turned off the car and turned to look at Stiles for the first time since they'd left the motel. Stiles only managed to keep his piercing gaze for a few moments before he slid out of the claustrophobic space and leaned against the hood of the Camaro, crossing his arms over his chest. Derek joined him only seconds later and although Stiles wanted to preserve a hint of his cool, didn't want to reveal the desperation clawing at his chest, the instant Derek laid his palm on his cheek, he looked up into his eyes and he was done for. 

"Will you be back?" he asked, slowly uncrossing his arms and slipping his hands into his pocket. After one of the longest seconds of Stiles' life, Derek nodded once. 

“Maybe someday,” he asked and Stiles forced himself to ignore that Derek's hesitation and the way his gaze briefly flicked away practically screamed that he was lying. Before Derek could move away again, before he was gone (forever), Stiles seized the collar of his leather jacket and kissed him as hard as he could, holding Derek there until he couldn't breathe. Once he pulled away, Derek leaned in for one last, lingering peck before he stepped away but before he returned to the driver's side of the car, he slipped his jacket off and, without hesitation, draped it around Stiles' shoulder.

“Looks better on you anyways,” he said quietly and Stiles knew that was an outright lie but he really, really didn't care. 

“Thank you,” he managed to say, clearing his throat to get the hoarseness out of his voice. “Promise I'll take care of it.” Derek just smiled at him, although the expression didn't reach his eyes and after running his hands down Stiles' chest, he was gone, sliding into the driver's seat and peeling out of the driveway like he was on a deadline. Stiles stood there for another minute, fingers clutching at the jacket, inhaling the sharp scents of leather and smoke that were engrained in the fabric. As soon as he could no longer hear the Camaro in the distance, he headed inside. 

Time passed, as time often does. Summer turned into junior year, which turned into senior year, which turned into freshman year all over again. Throughout that time, Stiles had a few relationships, which didn't pan out into anything. He did become an expert on the subject though because Scott, Allison and Issac were constantly breaking up and getting back together (in some form or another) and helping them sort out their woes was practically a full time job. 

On senior prom night, after his friends took off to Scott's house, he slept with Danny and although he'd definitely gotten better since their fumbles in sophomore year, he couldn't knock the memory of Derek out of Stiles' head. Nothing succeeded at doing that, no matter how hard he tried, no matter how hard he attempted to convince himself that Derek didn't matter anymore.

He told himself that but, even though it was too big and made him look kind of ridiculous, he started wearing the leather jacket whenever he could. Even after he took a leap of faith and left Beacon Hills for college, he took it with him, sewing up its frayed seams and paying someone in his residence to fix the zipper when it broke. He wore it as often as he could because, even if he wasn't waiting around for Derek, he couldn't help but hope, hope that one day, he'd be walking down the street and there would be a voice at his ear saying _I think that's my jacket_ and Stiles would turn around and say _told you I'd take care of it._

He wasn't waiting. But until he found someone who interested him as much as Derek had, until he found someone who could help him forget, he refused to give up hope.

**Author's Note:**

> So, long ago when I was 15, I used to write RPF. I haven't done that in years but while I was going through my old stories on the writing site I used to use, I came across one of my stories that I quite liked the concept for. That story (also called Leather & Alcohol) formed the basic premise and outline of this story but it was changed _a lot._ I just thought I'd let you all know that. (:


End file.
